Ethyl Acetate → 4'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

HRID 2048588Notes

Reaction equation

HRID 2048588 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:3].N12CCCN=C1CCCCC2.[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH:43]([C:49](=O)[CH2:50][CH2:51][CH3:52])[C:44](OCC)=[O:45])=[CH:38][CH:37]=1)#[N:29].C(OCC)(=O)C>CCN(C1C=CC=CC=1)CC.O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:44](=[O:45])[C:43]([CH2:42][C:39]3[CH:40]=[CH:41][C:36]([C:31]4[C:30]([C:28]#[N:29])=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:37][CH:38]=3)=[C:49]([CH2:50][CH2:51][CH3:52])[N:16]3[N:15]=[CH:14][CH:13]=[C:12]23)=[CH:9][CH:10]=1)[CH3:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67009388N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine

Product 1

HCID 670091114'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7061N,N-DiethylanilineSolvent

Procedure

N-[4-(1-Methylethoxy)phenyl]-1H-pyrazol-5-amine (0.37 g) and a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.051 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (1.2 g) in diethylaniline (5 mL) were stirred at 180° C. for 1 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.76 g, 89%).

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8c9f62b72574521afe3184dd64446ab
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

Loading…